


I Like You Both Ways

by CastheNerdfighter



Series: Both Ways [1]
Category: Supernatural
Genre: Alternate Universe - College/University, Bisexual Dean Winchester, Castiel Does Not Care About Gender Norms, Castiel and Gender, Dean is a flirt, Dean is an oblivious idiot, Fluff, Genderfluid Castiel, Happy Ending, M/M, Miscommunication, Not really nsfw, Openly Bisexual Dean Winchester, Other, Romantic Comedy, just a little hot and heavy car make out sessions
Language: English
Status: Completed
Published: 2017-08-11
Updated: 2017-08-11
Packaged: 2018-12-13 21:32:18
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,270
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11768802
Author URL: https://archiveofourown.org/users/CastheNerdfighter/pseuds/CastheNerdfighter
Summary: Based off of a tumblr prompt:"A romantic comedy where the main character meets a guy and really likes him, then later on meets a girl they also like, and they are tearing themselves up trying to choose between the two, only to find out in the end that they were the same, genderfluid, person."





	I Like You Both Ways

**Author's Note:**

> I am a nonbinary individual, and I use they/them pronouns. I wrote this fic from Dean's point of view, so he uses pronouns to fit how Cas is presenting themself. In the end he realizes he misgenders Cas, and switches to using they/them pronouns. If I write the wrong pronouns, or write any mistakes about Cas' gender-fluidity, please let me know! I am going with Cas identifying as both male and female, and presents themself depending on the day.

"Dean, this is Castiel. Cas, this is Dean," Sam introduced.

God, Dean wished this would be over. Sam had been practically throwing guys at him since he came out to him last year. Just because someone is gay, doesn't mean Dean will like them. 

"How are ya," Dean muttered, reaching out a hand to shake. The man looked nervous, and his hand was clammy.  _Weird, why is he nervous about meeting me?_  Dean thought. Then he looked up.

 _Son of a bitch._  Or did he say that outloud? By Sam's raised eyebrows it appears he did. "Uh, I mean, damn it, I forgot... to uh... check something."  _Smooth, Winchester._

"It's a pleasure to meet you," the man said. His gaze was focused solely on Dean, so he almost jumped when Sam touched his shoulder.

"Woah, Cas, I'm just getting us some beers." Sam gave Dean a look. "Behave while I'm gone."

"You behave while I'm gone," Dean muttered at Sam's back. "Sorry about him. He thinks if he throws enough guys at me, I'll fall in love or some shit."

Cas nodded absently. "Dude, I'm kidding." Dean squinted at the man sitting across from him.

He was one of the stranger finds Sam had dug up. All Dean had retained of the lengthy monologue Sam had given him in the car was that he was Sam's TA last semester and a good friend of his. And he was queer. Or something. He didn't remember.

Now he wished he'd paid more attention. The guy was... striking. Black hair spiked just so, giving him an aloof air. But his trench coat, which he hadn't taken off, and suit gave him a studious air, like he could command attention. He certainly had Dean's attention.

But that  _stare_. Dean had known the guy all of five minutes and he didn't think the guy had blinked or looked away once. He cleared his throat awkwardly. "Ahem. So, Sam said you're a TA at KU? Do you live in the area?" Most of the students from Dean's classes were locals, but Dean couldn't remember seeing Cas before.

"I'm from farther south in Kansas. I'm a graduate student, and I know Sam's history professor from my undergraduate years. I've been Balthazar's TA for some years."

"The guy honestly gives me the heeby jeebies. I couldn't tell if he was hitting on me or wanted to eat me." Dean laughed, but Cas just squinted his eyes at Dean.

"I don't think he's a cannibal, but I'll admit that he can be quite... flirtatious."

"That's not what I meant-" Dean started, but gave up when Sam arrived with an arm full of beers.

"So, how's everything going?" Sam gave Dean a wide eyed look, which Dean ignored in favor of grabbing a beer from the table and gulping down the better half of it. "Alright. So Cas, what are you plans for the summer?"

They chatted for a little bit. Cas went to the bathroom but wasn't gone long enough for Sam to properly interrogate Dean. When Sam left to get a second round, an awkward silence filled the booth. Well, it wouldn't be so awkward if Cas wasn't staring so intently at him.

All in all, it wasn't the worst set up Sam had ever tried. He grimaced when he remembered Sam introducing him to Benny, who he'd already dated and hadn't exactly left things on good terms. Awkward wasn't the half of it.

They parted ways and Dean didn't give the poor guy a second thought. It wasn't like they were ever going to see each other again.

* * *

But fate has a way of throwing things Dean's way when he's too stupid to run after them himself.

In this case, it meant Dean running into the guy  _everywhere._

At the grocery store buying eggs from Happy Chickens.

At the farmer's market with Sam, buying kale and some other made up sounding vegetables.

At school: around every corner he turned he seemed to find the guy. In the coffee shop, the library, even talking to his professors. 

After a month of this nonsense, Dean confronted the guy as they waited in line at  _The Lila Bean,_  his favorite place to get coffee. And run into Cas.

Okay, maybe it was time to admit that Dean was kinda crushing on the guy.

"Thanks, Gabe," Cas muttered as he took his coffee from the barista.

"No problem, bro," the cashier winked at Dean, and Dean managed to catch Cas rolling his eyes.

"Do you know him?" Dean asked. He hadn't recognized the barista, since he usually only got coffee in the mornings. Now he'd taken to stopping by for an iced coffee after lunch, when he knew Cas would be there.

"He's my idiot little brother. Who, for some reason, decided it would be a good idea to crash with me this summer. I told him he has to work, and he took it to mean at my favorite coffee joint." Cas sighed. "Sorry, I don't mean to unload on you."

"Hey it's no problem," Dean reassured.  _I wish you'd tell me more about yourself._

Cas continued, playing with his straw, swirling his drink. "He's going here in the fall, but he managed to graduate high school early, and I understand that he doesn't want to be home. Hell, I moved out the second I graduated, I get it." Cas sighed again. "I just wish he could be away from home... and not  _here_."

"Hey, I totally get you. Sam only goes here because it's local and cheaper for being in state. If I could have my way, my baby bro would be at Stanford or some fancy college for that big brain of his." Dean loved his brother, and often worried that he wasn't going to succeed because they didn't have enough money to send him to a better school.

They chatted a bit more about the end of the semester, and Dean's impending graduation (Cas still had one more year of graduate school), and Dean slowly built up the courage to... what? Ask the guy out? Tell him he had big old love eyes for him? He barely knew the guy, and yet he was head over heals for him.

No, he'd wait. Get to know him better. And what better way to do just that than ask for his number. Dean opened his mouth to ask Cas for his digits with a cheesy line like, "I lost my phone number, can I have yours?" when Cas abruptly got up.

"Shit, shit," Cas muttered as he gathered his coat and bag, haphazardly pushing in his chair. "Sorry, Dean, I forgot I have a meeting with my advisor right... now. Shit."

 _Damn, that's hot,_  Dean thought as he watched Cas walk away, well, more like strut his way out of the coffee shop. It was only after the bell on the door announced he'd left that Dean realized he'd forgotten to ask for Cas' number.

_Son of a bitch._

* * *

As graduation approached, Dean didn't see Cas much. Dean didn't see anyone much, which was probably why Charlie threw a lavish party the weekend after graduation. He already had a job lined up for the next fall, and he had one last free summer to look forward to. As well as student loans to pay off...

 _No, I graduated, I can be proud of that. Suck it Dad,_  Dean thought at the sky. In that moment he didn't even feel bad about the internalized homophobia or any of the shit his Dad had instilled in him. He was gone, and Dean was free of him. Free to do whatever he wanted, whomever he wanted.

Which apparently was to be another setup. This time by Charlie.

"Dean, this is Cassie. Cassie, Dean," Charlie introduced.

Another day, another poor idiot being thrown his way. By now he just lets them down easy, apologizing for his crazy friends.

"How are ya," Dean muttered. 

"Charlie, I don't-"

"Nonsense, you'll love Dean! He's hot but he's harmless, I can say that as a fellow gay. Now, go be gay together!" Charlie practically shoved the two of them together, running back to the bar to meet up with Dorothy.

There was something familiar about the girl, but Dean couldn't quite place it. "So, you're name's Cassie?"

"Um... yes?"

 _Okay, what is it about weird people named Cas? Oh, wait!_  Dean thought, and he could imagine a light bulb glowing above his head.  _She reminds me of Castiel. I wonder if she knows him..._ Dean thought absently. He was getting a little distracted by Cassie's skirt, which she was picking at nervously.

"Hey, how about we go dance?" Dean loved to dance, and he was tipsy enough to not care about his lack of skill. Ash was DJ in the club tonight, so of course as soon as Dean dragged Cassie to the dance floor, he put on a sappy love song. The kind Dean pretended he didn't sing along to in the car.

"Fuck you!" Dean shouted over the music. "Sorry, Ash is an ass."

"That's alright," she responded. Or Dean thought she did. Her lips were moving but it was too loud to hear. Instead, he grabbed her hand and waist, and led her around the dance floor in a mock-waltz. She laughed, open and free, and Dean could feel himself starting to like this girl.

The only problem was... Cas.

Was it wrong that Dean already liked another person? Could he have two crushes at once? He didn't think he could handle that, frankly. Did he just like this girl because she reminded him of Cas? It was all very confusing to Dean, so he decided to drown out the thoughts with the music, just enjoying the gentle sway of the sappy music. When Charlie gave him a thumbs up from the bar, he flipped her off (discretely, of course), and returned his gaze to Cassie.

 _Son of bitch,_  Dean thought. Or said. But this time, if his thoughts escaped his head, it was too loud for her to hear.

By the end of the night, Dean had almost forgotten about Castiel. When they finally stumbled out of the club, it way past midnight and they definitely drank far too much beer. He asked her address and called them a cab.

And if they made out in said cab on the way home, Dean's not one to kiss and tell.

* * *

Dean was conflicted. On the one hand, he had an awesome time with Cassie. On the other, he'd only just met her, and he'd known Castiel for... okay, only a month or so. They were both practically strangers, and he had crushes on them both.

It didn't really matter anyway. He didn't have either of their numbers, so it was up to Sam and Charlie if he saw either of them again. Dean wondered once more of the chances of two people named Cas living in the same town and not knowing each other, but then he started thinking about statistics and his head hurt. He much prefered thinking about engines.

Speaking of, he was currently deep inside of one. Which was why he didn't hear Bobby yell at him that he had a visitor.

"Dean? Dean," a faint voice trickled over the loud Led Zeppelin from Dean's earbuds. Dean almost hit his head on the car hood but managed to make his snafu look planned.

"Hey, how can I help - oh, hey, Cassie!" Dean blushed, remembering the last time he'd seen her. He'd been a perfect gentleman, walking her to her door, and not asking for her number. What an idiot.

"Hello, Dean," she said. If her voice was a little deeper today, he chalked it up to mornings. He knew his voice was at least an octave deeper before noon.

"How, how are you?" Dean stumbled.  _Keep it together, man._

"I'm great. Well, actually, I'm not so great. I mean, _I'm_ fine, it's my car that isn't doing so great. Not that cars have feelings, but if they did-"

"Woah, girl, slow down! Your car is... broken down?"

Cassie nodded gravely. "It won't start. I had it towed and Mr. Singer mentioned your name, so I thought I'd come see you. And ask you to look at my car. Mr. Singer left, I don't know where he went."

"Bobby, you sly dog," Dean grinned, not bothering to hide it. Bobby never threw him a bone like this. Cassie must have made one hell of a first impression. "So, where's this car of yours?"

Dean laughs when Cas showed him her car. " _This_ is your car?" Dean did his best to school his laughter under Cassie's glare, but he only laughed harder. Finally, Cassie chuckled a little bit. 

"It's actually my... brother's. Or, well, it used to be my father's. I don't usually drive, but of course it had to break down the one day I needed it."

"Do you need a ride somewhere?" Dean asked, already wiping his hands off, prepared for any excuse to show Cassie the Impala.

"Um, not anymore, I was going to go meet up with Charlie, but then I called and told her the car broke down. We rescheduled."

Dean nodded, maybe for a bit too long, but Cassie didn't seem to notice.

"Dean, you don't have to fix it right now-"

"Hey now, it's the least I can do! Now let's take a look." Dean opened up the hood of the car and found the problem, getting to work while Cassie watched. It was a simple issue, one that should have been easily preventable, had she known anything about cars. But if was a good opportunity for his to show off his skills (and his ass), and after half an hour under the hood, he was finished.

"Aaaaand, done!" He said with a flourish.

"Wow, Dean, that was fast!" Cassie clapped, and he couldn't tell if she was genuine or sarcastic.

"Now, do you wanna see a  _real_ car?" Dean said, washing his hands in the big basin sink. Cassie just raised her eyebrows, glanced over at the still-empty reception area, and shrugged her shoulders. "This way, milady."

Dean led her back through the  _employees only_ door, knowing the way by heart. He'd been working at Bobby's garage during summers since... since he could pick up a wrench, it seemed like. And he'd been restoring his dad's 1967 Chevy Impala almost as long. 

She sat in full glory in the back parking lot, under a small awning to protect her from the weather. It sat next to several of Bobby's old junkers and a VW van that looked just like the Scooby Doo van. He hated that old thing. He much prefered his baby.

"This is my baby, I built her from the ground up after the... accident," Dean introduced. When Cassie gave him a wide-eyed look, he hastened to explain that it was a long time ago, before he graduated from high school. He admitted that the crash had killed his father, but had only given him and Sam a few broken bones. She still looked sad, so he changed the subject.  _Keep on target, man._

"Would you like to take a look?"

Cassie grinned. "Hell yes."

Dean pointed out things that Cassie pretended to understand, spouting factoids and stats about her. How fast she could go, pretty much her entire history.

"She's beautiful," Cassie concluded, running her hand along the front.

"You're more beautiful," Dean murmured. He inched closer, glancing around. They were alone back there, and no texts from Bobby were buzzing in his back pocket.

"What's that?" Cassie asked.

"You're beautiful. May I kiss you?" Dean felt emboldened, and incredibly turned on. And if Cassie's frequent glances to his lips were any indication, so was she.

"You may."

Somehow Dean managed to open the back door, and Cassie pushed him back into the car, where he stretched along the seat. It was broad daylight, but they were hidden under the awning. He let her set the pace, which seemed to be climbing on top of him and kissing him breathless.

She remained on top of him for several minutes as they kissed. He ran his hands along her, but when he tried to slip his hands under her sweater, she batted him away.  _Alright, above the clothes it is_. That still gave him plenty to explore, and soon enough he was running his hands through her short hair, her beanie lost to the floor of the car.

He knew his time was running out, and Bobby would come find them soon, so Dean made a bold move. He inched closer to the edge of the seats, and flipped them so he was on top. When Cassie reached up to meet him for a bruising kiss, Dean accidentally brushed his hips against hers. 

And felt a hard cock against his own.

Dean had been with enough guys to recognize a growing bulge in the pant situation. And Cassie was having one.

In his best attempt not to freak her out, Dean pecked a kiss to her lips and sat up. She sat up to, reaching to kiss him again, but he stopped her.

"Cassie, um, are you trans?"

She looked taken aback, almost ashamed. She looked away. "Um, yes?"

"I'm sorry, that was way too personal of me to ask. I don't want to make you uncomfortable."

"That's alright. I really should have told you."

"When? After we made out in the taxi? Or when I was elbow deep in your car?"

Cassie chuckled. "I guess you do have a point."

"I'm bisexual, so I'm cool with whatever your gender is. But I gotta say,  _damn girl_ , you are super hot. I had no idea." Dean knew he was being somewhat patronizing, but Cassie didn't seem to mind, preening under the attention.

"I do have one more thing to tell you, Dean," Cassie began, looking up from under her lashes.

"Well, unless you're an alien too, I don't think you can give me any more surprises." Dean laughed.

But before she could tell him anything, Bobby appeared at the back door. He marched right up to the Impala and pointedly knocked on the window. "You _are_ still at work, Dean."

"Sorry, Bobby!" Dean shared a scared look with Cassie, but Bobby just  _humph_ ed and walked back inside. "Ha, we should probably get you back on the road, right?"

"Yeah." They scrambled out of the car, which Dean realized was actually quite warm in the summer heat. "Um, do you want to go out sometime, Dean?"

"I'd love that, Cassie." Dean pulled out his phone, pressing the button to add a new contact. "When are you free?"

They made plans for that Friday night. She was a TA at KU for a summer course, so he agreed to pick her up after the class. He refused her attempts to pay him for the car repair and towing, citing that she could "make it up to him this friday" with a wink. As he waved goodbye and watched her drive down the road, Bobby came up behind him and punched him in the arm.

"What?"

"Don't mess that up, boy. She's a catch. Don't let her go."

"I won't!"

"... Okay. Idjit."

* * *

By the time friday came around, Dean had almost forgotten about Castiel. _Almost_.

When Cassie told him she was a TA at KU, it reminded him of a certain someone, a certain crush, that he hadn't seen for a while. Sam hadn't mentioned him for a while, and Dean had no reason to bring him up. Dean just assumed he'd never see him again. He was bummed, but he had Cassie now, and like Bobby said, she was a catch. He didn't intend to let her go for a crush he hadn't seen in months.

Which was his logic until he pulled up to the Humanities building on KU campus. It was the middle of summer session; what were the chances Castiel was also a TA this summer, or had a class this late on a friday? In this very building?

Apparently very high, because as Dean glanced at his phone for the millionth time to check the classroom number, he ran right into... Gabe.

"Heya, Dean-o! Heard about your hot date tonight. Looking good! Cas is getting laid to-o-night!" The man shouted as he made his way down the hallway past Dean.

"What." Dean spoke to empty air, the younger man was long gone.

Letting the weird interaction slide off him, Dean made his way down the hall. 230, 240, ah, 250. Dean took a deep breath and checked his hair in his phone before opening the door.

To find Cas.

He was talking to another man, probably the professor, and erasing the whiteboard. A third person, a woman in a dress, got up from her seat in the front row and made her way to the door. Since she was the only female in the room, Dean made to greet her. But she pushed past him and left, and he realized he hadn't recognize her.

Further baffled, Dean entered the room and decided to say hello to Cas while he waited for Cassie. "Hey, Cas!"

"Hello, Dean," Cas replied. He said goodbye to the older man, who merely glanced at Dean. Professor Balthazar, Dean recognized. The professor obviously didn't remember him, because he left without comment. 

"You're early," Cas continued.

"What?" 

"I said, you're early. I texted for you to come at 5:15."

"It is 5:15," Dean managed, holding out his phone for Cas to see the time. Cas glanced up at the wall, where a clock said 5 pm.

"Oh dear, I better fix that." 

Dean could only watch, baffled, as Cas got a chair and retrieved the clock, setting it forward 15 minutes. "I bet it was those freshmen again. Trying to make me look late."

"Uh, huh." Dean said absently. Sometime wasn't right about this situation.

Cas put away the chair and grabbed a purse from under the front desk. It was a simple black canvas bag, more a laptop bag than purse. But still, seeing Cas hold the purse, and pull out the phone exactly like Cassie's...

Everything clicked into place at once.

Cassie was trans.

Cassie might not be out everywhere.

Such as at school.

Which means she presented as a man at school.

A man such as Castiel...

Who Dean had a big ol' crush on.

As soon as the thoughts connected in Dean's head it was obvious. Dean sat there stunned, trying to wrap his head around the whole situation. His theory was furthered proved when Cas pulled out a silky red dress from the back, and a pair of flats.

"I was going to go to the bathroom, but then you had to come early," Cas said, like it was perfectly normal for him to be  _Cassie_.

"I can turn around." Dean did just that. They were on the second floor, and it was a friday afternoon in summer. There was no one else around to see.

Dean felt a tap on his shoulder, and when he cautiously turned around, Cas' back was to him. 

"Zip me up?" Cas asked. Dean complied, and when Cas turned around, he looked worried. "Dean, please don't be mad. I was going to tell you, I tried to tell you. Actually, Sam said he told you."

"Told me what?" Dean was very confused.

"I'm genderfluid."

"I thought you said you were trans."

"I am trans. That just mean I identify as a gender that differs from my assigned gender. I was assigned male at birth, but I identify as genderfluid, which roughly means I'm both genders. Or neither. It depends."

"It depends."

"Yes, most days I feel male, and present masculinely." Cas picked up their dress shirt and folded it up, slipping it into the purse. "And other days I feel female, and present femininely." They gestured to the red dress that hugged their hips and floated to their knees.

"Okay. Okay, I understand, I think. I'm sorry, this is just so new to me. What am I supposed to ask? Oh, right, um, what pronouns do you use?"

Cas looked happy to be asked that. "I usually use they/them, but you can use whatever you want, Dean. Whatever makes you feel comfortable."

"Me, comfortable? Cas, I should be making  _you_ feel more comfortable. I'd be a terrible date if I didn't." Dean took both of Cas' hands in his own. "I can't believe I kissed you. I mean, I kissed Cassie, but I was also kissing  _Castiel._ " Dean looked at the person in front of him in awe.

"I know, it was a little deceitful of me to keep that from you. But I hadn't seen you as Cas in so long, I thought you'd forgotten about me." Cas looked away, but Dean slipped a hand up to cup their face.

"Cas, you don't get it. I had a big old crush on you. And I felt bad about having a crush on two people at once. I felt like I was betraying you, but in the end I just liked you both ways. I want to know everything about you, Cas. If you're willing to put up with my nonsense."

"Well, that sounds like a deal I can't afford to pass up." Cas laughed. Dean decided he loved their laugh, loved their smile. Loved them.

"Now, where are we going for dinner?"

**Author's Note:**

> Again, if I made a mistake let me know!
> 
> Leave some love with kudos or a comment! It will make my day :)


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